Abstract
The reaction of direct hydroalkoxylation of norbornene in the presence of H-beta zeolite catalyst has been studied. It has been found that the selectivity for exo-alkoxynorbornanes of the reaction of norbornene with monohydric alcohols (saturated, unsaturated, or aromatic) reaches 98% at a conversion of 78–98% of the unsaturated compound. The reaction of norbornene with diols (ethylene glycol and 2-butene-1,4-diol) in the presence of H-beta zeolite affords mono- and diethers, whose yield and ratio can be controlled by varying reaction parameters.
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References
R. McCague, M. G. Rowlands, S. E. Barrie, and J. Houghton, J. Med. Chem. 33, 3050 (1990).
J. M. Hanifin, S. C. Chan, J. B. Cheng, et al., J. Invest. Dermatol. 107, 51 (1996).
M. K. Mamedov, I. N. Gadzhieva, and Kh. M. Alimardanov, Russ. J. Org. Chem. 39, 180 (2003).
M. K. Mamedov and E. T. Suleimanova, Zh. Org. Khim. 29, 1138 (1993).
A. F. Plate and T. A. Meerovich, Izv. Akad. Nauk SSSR, No. 2, 219 (1947).
H. C. Brown and M.-H. Reie, J. Am. Chem. Soc. 24, 5646 (1969).
S. A. Shackelford, J. Org. Chem. 44, 3485 (1979).
D. F. Shellhamer, C. M. Curtis, R. H. Dunham, et al., J. Org. Chem. 50, 2751 (1985).
D. F. Shellhamer, R. D. Chapman, S. A. Shackelford, et al., J. Chem. Soc., Perkin Trans. 2, No. 2, 787 (1997).
M. J.-L. Tschan, C. M. Thomas, H. Strub, and J.-F. Carpentier, Adv. Synth. Catal. 351, 2496 (2009).
A. G. Gasanov and A. V. Nagiev, Zh. Org. Khim. 30, 707 (1994).
D. C. Rosenfeld, S. Shekhar, A. Takemiya, et al., Org. Lett. 8, 4179 (2006).
R. T. Mathers, C. LeBlond, K. Damodaran, et al., Macromolecules 41, 524 (2008).
J. G. Taylor, N. Whittall, and K. K. (Mimi) Hii, Chem. Commun., Issue 40, 5103 (2005).
M. J.-L. Tschan, C. M. Thomas, H. Strub, and J.-F. Carpentier, Adv. Synth. Catal. 351, 2496 (2009).
T. Hirai, A. Hamasaki, A. Nakamura, and M. Tokunaga, Org. Lett. 11, 5510 (2009).
Y. Oe, T. Ohta, and Y. Ito, Synlett, No. 1, 179 (2005).
T. T. Dang, F. Boeck, and L. Hintermann, J. Org. Chem. 76, 9353 (2011).
K. Hensen, C. Mahaim, and W. F. Hölderich, Stud. Surf. Sci. Catal. 105, 1133 (1997).
S. Radhakrishnan, J. Franken, and J. A. Martens, Green Chem. 14, 1475 (2012).
G. Z. Raskil’dina, A. M. Suleimanova, A. N. Kazakova, et al., Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. 56(10), 29 (2013).
G. Z. Raskil’dina, Yu. G. Borisova, E. A. Mustafina, and N. G. Grigor’eva, in Low-Waste, Resource-Saving Chemical Technologies and Environmental Safety: Proceedings of All-Russia Scientific-Practical Conference with International Participation (Fobos, Sterlitamak, 2013), p. 29 [in Russian].
J. K. Whitesell and M. A. Minton, Stereochemical Analysis of Alicyclic Compounds by C-13 NMR Spectroscopy (Chapman and Hall, London, 1988).
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Original Russian Text © G.Z. Raskil’dina, A.M. Suleimanova, A.N. Kazakova, N.G. Grigor’eva, B.I. Kutepov, S.S. Zlotskii, 2015, published in Neftekhimiya, 2015, Vol. 55, No. 2, pp. 162–170.
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Raskil’dina, G.Z., Suleimanova, A.M., Kazakova, A.N. et al. Products of direct hydroalkoxylation of norbornene with alcohols over H-beta zeolite catalyst. Pet. Chem. 55, 154–162 (2015). https://doi.org/10.1134/S0965544115020164
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DOI: https://doi.org/10.1134/S0965544115020164